58-55-9Relevant articles and documents
Coordination polymers as potential solid forms of drugs: Three zinc(ii) coordination polymers of theophylline with biocompatible organic acids
Lou, Benyong,He, Fengdan
, p. 309 - 316 (2013)
The biocompatible organic acids such as acetic acid (Hac), benzoic acid (Hbz) and nicotinic acid (Hnit), have been employed as second ligands to assemble biocompatible coordination polymers of theophylline (Hthp), respectively. As a result, three coordination polymers [Zn2(thp) 2(ac)(OH)]n (1), [Zn2(thp)2(bz)(OH)] n (2) and [Zn(thp)(nit)]∞ (3) have been synthesized through hydrothermal and mechanochemical reactions. Theophylline could be released rapidly in simulated gastroenteric fluid (phosphate-buffered solution, PBS) and slow release of theophylline could be achieved from the three polymers in pure water at 37 °C with continuous stirring.
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Kostareva et al.
, (1976)
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Isolation and characterization of 1,3-dimethylisoguanine from the Bermudian sponge Amphimedon viridis
Mitchell,Whitehill,Trapido-Rosenthal,Ireland
, p. 727 - 728 (1997)
The new compound 1,3-dimethylisoguanine has been isolated and characterized from the Bermudian sponge Amphimedon viridis. Chemical conversion of the natural product to theophylline and 2D NMR methods were used to determine the position of the methyl groups on the purine ring. Analysis of the mass spectral fragmentation pattern allowed assignment of the purine ring as isoguanine.
SERS multiplexing of methylxanthine drug isomersviahost-guest size matching and machine learning
Chio, Weng-I Katherine,Dinish, U. S.,Jones, Tabitha,Lee, Tung-Chun,Liu, Jia,Olivo, Malini,Parkin, Ivan P.,Perumal, Jayakumar
supporting information, p. 12624 - 12632 (2021/10/06)
Multiplexed detection and quantification of structurally similar drug molecules, methylxanthine MeX, incl. theobromine TBR, theophylline TPH and caffeine CAF, have been demonstratedviasolution-based surface-enhanced Raman spectroscopy (SERS), achieving highly reproducible SERS signals with detection limits down to ～50 nM for TBR and TPH, and ～1 μM for CAF. Our SERS substrates are formed by aqueous self-assembly of gold nanoparticles (Au NPs) and supramolecular host molecules, cucurbit[n]urils (CBn,n= 7, 8). We demonstrate that the binding constants can be significantly increased using a host-guest size matching approach, which enables effective enrichment of analyte molecules in close proximity to the plasmonic hotspots. The dynamic range and the robustness of the sensing scheme can be extended using machine learning algorithms, which shows promise for potential applications in therapeutic drug monitoring, food processing, forensics and veterinary science.
Synthesis of a new class of bisheterocycles via the Heck reaction of eudesmane type methylene lactones with 8-bromoxanthines
Patrushev, Sergey S.,Rybalova, Tatyana V.,Ivanov, Igor D.,Vavilin, Valentin A.,Shults, Elvira E.
, p. 2717 - 2726 (2017/04/14)
The eudesmane-type methylene lactones (isoalantolactone, alantolactone, 4,15-epoxyisoalantolactone, 2′,2′-dichloro-4H-spiro[cyclopropane-1′,4-eudesma-11(13)-en-8β,12-olide], and alantolactone) react with 8-bromoxanthines (8-bromocaffeine, 8-bromotheobromine, 8-bromo-3-butyltheobromine, 8-bromotheophylline, 8-bromo-9-butyltheophylline) under Heck reaction conditions to produce the target (E)-13-(2,6-dioxo-2,3-dihydro-1H-purin-8-yl)eudesma-4(15),11(13)-dien-8β,12-olides and the subsequent endocyclic isomers - 11-(2,6-dioxo-2,3-dihydro-1H-purin-8-yl)-13-normethyleudecma-4(15)-7(11)-dien-8α,12-olides. It was revealed that the yield and product ratio depends on the reaction conditions and the structure of methylene lactone. The effectiveness of Pd(OAc)2–caffeine catalytic system has been demonstrated in this reaction. The electric eel acetylcholinesterase inhibitory activity of the eudecmanolide-xanthine hybrids was evaluated. Among the new type bisheterocycles compound 27 with butyl and 2-oxodecahydronaphtho[2,3-b]furan-3(2H)-ylidene)methyl substituents at C-7 and C-8 of the xanthine core showed moderate activity with IC50 value of 40?μM.
A method of synthesis of theophylline
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Paragraph 0027; 0028; 0032, (2016/10/08)
The invention discloses a method for synthesizing theophylline. The method comprises the following steps: performing a methylation reaction on dimethyl sulfate, 6-aminouracil and a sodium hydroxide solution; adding formic acid for a carboxylation reaction; adding a mixed acid solution formed by mixing fuming nitric acid and concentrated sulfuric acid at a volume ratio of (0.8-1.1):(0.9-1.2), and performing heating reflux for a nitrosylation reaction; and finally, adding iron powder and anhydrous acetic acid for a cyclization reaction to obtain theophylline. According to the method disclosed by the invention, the yield is greatly higher than that of the prior art, the operation process is simple, and the reaction conditions are simple.
